185116-43-2

Basic information

• Product Name: FMOC-4-AMINOBENZOIC ACID
• Synonyms: FMOC-PABA-OH;FMOC-P-ABZ-OH;FMOC-4-AMINOBENZOIC ACID;FMOC-4-ABZ-OH;4-(FMOC-AMINO)BENZOIC ACID;4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINO-BENZOIC ACID;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-4-AMINOBENZOIC ACID;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-P-AMINOBENZOIC ACID
• CAS NO: 185116-43-2
• Molecular Formula: C₂₂H₁₇NO₄
• Molecular Weight: 359.37
• Product Categories: FMOC;Amino Acids;Unusual Amino Acids
• Mol File: 185116-43-2.mol

Chemical Properties

• Melting Point: ~277 °C (dec.)
• Boiling Point: 544.854 °C at 760 mmHg
• Flash Point: 283.318 °C
• Appearance: /
• Density: 1.352 g/cm³
• Vapor Pressure: 1.05E-12mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: 2-8°C
• PKA: 4.29±0.10(Predicted)
• BRN: 7722986
• CAS DataBase Reference: FMOC-4-AMINOBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-4-AMINOBENZOIC ACID(185116-43-2)
• EPA Substance Registry System: FMOC-4-AMINOBENZOIC ACID(185116-43-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 185116-43-2(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
FMOC-4-AMINOBENZOIC ACID is used as a monomer in the improved rapid synthesis of oligo(benzamide) block copolymers. Its incorporation into these polymers enhances their structural diversity and functional properties, making them suitable for various applications in materials science and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, FMOC-4-AMINOBENZOIC ACID is used as a protecting group for the synthesis of various drugs and bioactive compounds. Its ability to protect specific functional groups during chemical reactions allows for the selective modification of target molecules, leading to the development of more effective and targeted therapeutic agents.
Used in Chemical Research:
FMOC-4-AMINOBENZOIC ACID is also utilized in chemical research as a versatile reagent for the synthesis of complex organic molecules. Its unique chemical properties enable the development of novel synthetic routes and methodologies, contributing to the advancement of organic chemistry and the discovery of new compounds with potential applications in various fields.

InChI:InChI=1/C22H17NO4/c24-21(25)14-9-11-15(12-10-14)23-22(26)27-13-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-12,20H,13H2,(H,23,26)(H,24,25)

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 52407-60-0 dimethyl N-(4-amino-benzoyl)-L-glutamate 
• 218603-30-6 N-<4-carbonyl>pyridin-2-ylmethyl)>aminobenzoyl>-L-glutamate 
• 218603-08-8 dimethyl N-<4-benzoyl>-L-glutamate 
• 1011719-40-6 C₂₉H₂₇N₃O₅ 
• 1011719-43-9 C₃₅H₃₈N₄O₆ 
• 1011719-39-3 C₂₉H₂₇N₃O₅ 
• 1031755-95-9 pentafluorophenyl 4-[(9H-fluoren-9-yl)methoxycarbonylamino]benzoate 
• 873113-34-9 4-(2(R)-benzoylamino-3-naphthalen-2-yl-propionylamino)-N-hydroxy-benzamide 

Relevant articles and documents

Solid-phase synthesis of coralmycin A/epi-coralmycin A and desmethoxycoralmycin A

The total synthesis of the natural product coralmycin A/epi-coralmycin A, as well as a desmethoxy analogue is described. Synthesis was achievedviaa divergent, bidirectional solid-phase strategy, including a key on-resinO-acylation,OtoNacyl shift, andO-alkylation protocol to incorporate the unusual 4-amino-2-hydroxy-3-isopropoxybenzoic acid motifs. The synthetic natural product was generated as a 1?:?1 mixture of epimers at the central β-methoxyasparagine residue and exhibited potent antibacterial activity against a panel of ten Gram-negative and seven Gram-positive organisms. The desmethoxy analogue possessed significantly more potent antimicrobial activity against this panel with minimal inhibitory concentrations (MICs) as low as 50 nM.

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives

A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof

The invention belongs to the technical field of medicines, and relates to a preparation method and medical application of an N1-aryl sulfanilamide-N4-beta-D-glucopyranose diamide compound. The compound is shown in a general formula (I), substituent groups are described in the specification, and the compound shown in the general formula (I) and an optical active body, a diastereoisomer and a pharmaceutically acceptable salt thereof are applied to preparation of anti-tumor drugs. Based on pharmacophore characteristics and subcellular localization of CA IX and XII, a selective CA IX and XII inhibitor is designed and synthesized, polyhydroxy high-polarity glucose is selected as a tail end, a classical pharmacophore aryl sulfanilamide fragment of a targeted CAs active center is introduced through a flexible aliphatic chain and a rigid aromatic structure, the overall structure can selectively inhibit catalytic activity of extracellular CA IX and XII, an anti-tumor effect is achieved, and therefore, the compound has a good application prospect.

Hydroxamic Acids Immobilized on Resins (HAIRs): Synthesis of Dual-Targeting HDAC Inhibitors and HDAC Degraders (PROTACs)

Inhibition of more than one cancer-related pathway by multi-target agents is an emerging approach in modern anticancer drug discovery. Here, based on the well-established synergy between histone deacetylase inhibitors (HDACi) and alkylating agents, we present the discovery of a series of alkylating HDACi using a pharmacophore-linking strategy. For the parallel synthesis of the target compounds, we developed an efficient solid-phase-supported protocol using hydroxamic acids immobilized on resins (HAIRs) as stable and versatile building blocks for the preparation of functionalized HDACi. The most promising compound, 3 n, was significantly more active in apoptosis induction, activation of caspase 3/7, and formation of DNA damage (γ-H2AX) than the sum of the activities of either active principle alone. Furthermore, to demonstrate the utility of our preloaded resins, the HAIR approach was successfully extended to the synthesis of a proof-of-concept proteolysis-targeting chimera (PROTAC), which efficiently degrades histone deacetylases.

Synthesis, biological evaluation, and docking studies of PAR2-AP-derived pseudopeptides as inhibitors of kallikrein 5 and 6

A series of protease activated receptor 2 activating peptide (PAR2-AP) derivatives (1-15) were designed and synthesized. The obtained compounds were tested on a panel of human kallikreins (hKLK1, hKLK2, hKLK5, hKLK6, and hKLK7) and were found completely i

Enzyme-triggered gelation: Targeting proteases with internal cleavage sites

A generalizable method for detecting protease activity via gelation is described. A recognition sequence is used to target the protease of interest while a second protease is used to remove the residual residues from the gelator scaffold. Using this appro

Tuning the solubility of hepta(p-benzamide)s via the monomer sequence

The automated synthesis of hepta(p-benzamide) heterosequences on solid support using a modified peptide synthesizer is reported. The oligomers are synthesized from 4-aminobenzoic acid and 4-amino-2-(hexyloxy)benzoic acid, the latter carrying a solubilizing hexyl side chain. It is known from previous studies that both the unsubstituted hepta(p-benzamide) and the fully hexyloxy-substituted hepta(p-benzamide) are insoluble in all common organic solvents. Heterosequences in which both types of monomers alternate are, however, soluble in polar organic solvents such as DMSO. The heterosequence heptamers behave as strong organogelators when DMSO solutions are left at room temperature for several hours. Transmission electron microscopic (TEM) investigations revealed that the gelation was due to the oligomers forming long entangled fibers via a non-covalent aggregation mechanism. We explain these phenomena by a heterosequence triggered switch of aggregation mechanism. The unsubstituted oligomers strongly aggregate via a directional hydrogen-bond driven mechanism which changes to a less directional π-interaction driven aggregation mechanism for the substituted oligomers. We hereby demonstrate that designed heterosequences in non-natural oligoamides can lead to materials with distinctly different conformations which directly affect the intermolecular interactions and their supramolecular organization.

A facile route to steady redox-modulated nitroxide spin-labeled surfaces based on diazonium chemistry

A TEMPO derivative was covalently grafted onto carbon and gold surfaces via the diazonium chemistry. The acid-dependent redox properties of the nitroxyl group were exploited to elaborate electro-switchable magnetic surfaces. ESR characterization demonstra

Synthesis of a tripodal scaffold for solid phase synthesis of artificial receptors

A convergent synthesis for the preparation of a new orthogonally protected tripodal scaffold has been developed. The scaffold was successfully coupled to a Tentagel solid support and further derivatised at the three attachment points demonstrating its possible use for combinatorial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

The Synthesis and Preferred Conformation of Pyridoyl Urea and Analogous Derivatives. Preparation of a Folate Analogue

The synthesis of 2-pyridoyl urea and analogous derivatives is reported. Also the synthesis of a folate analogue, containing 2-pyridoyl urea instead of the pterine moiety, is described. NMR Spectra show that the acylureas adopt an intramolecular H-bonded c